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EP0463513B1 - Benzylecétones et fongicides les contenant - Google Patents

Benzylecétones et fongicides les contenant Download PDF

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Publication number
EP0463513B1
EP0463513B1 EP91109806A EP91109806A EP0463513B1 EP 0463513 B1 EP0463513 B1 EP 0463513B1 EP 91109806 A EP91109806 A EP 91109806A EP 91109806 A EP91109806 A EP 91109806A EP 0463513 B1 EP0463513 B1 EP 0463513B1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
aryl
halogen
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP91109806A
Other languages
German (de)
English (en)
Other versions
EP0463513A3 (en
EP0463513A2 (fr
Inventor
Horst Dr. Wingert
Hubert Dr. Sauter
Franz Dr. Roehl
Reinhard Dr. Doetzer
Gisela Dr. Lorenz
Eberhard Dr. Ammermann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
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Publication of EP0463513A3 publication Critical patent/EP0463513A3/de
Application granted granted Critical
Publication of EP0463513B1 publication Critical patent/EP0463513B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to benzyl ketones, fungicides containing these compounds and methods of combating fungi with these compounds.
  • the object of the invention was to provide active ingredients and fungicides with a better action.
  • the new compounds of the general formula I can exist as both E and Z isomers, which can be separated in a conventional manner. Both the individual isomeric compounds and their mixtures are encompassed by the invention and are useful as fungicides.
  • X, R1, R2 and R3 have the same meaning as in formula I, Y means O; Hal in formula II, III is halogen, preferably bromine; Hal in formula IV is halogen, preferably chlorine.
  • the benzyl halides II are generally at temperatures from -5 to 10 ° C, preferably at 0 ° C with activated zinc (P. Knochel, MCP Yeh, SC Berk, J. Talbert, J. Org. Chem. 53, 2390, 1988) reacted.
  • activated zinc P. Knochel, MCP Yeh, SC Berk, J. Talbert, J. Org. Chem. 53, 2390, 1988
  • the reaction to the copper / zinc-organic compound with the tetrahydrofuran-soluble CuCN.2LiCl complex then takes place at temperatures from -80 to -10 ° C.
  • the reaction with the carboxylic acid halides IV takes place e.g. in an inert, anhydrous solvent, e.g. Tetrahydrofuran at temperatures from -70 to 30 ° C.
  • anhydrous solvent e.g. Tetrahydrofuran at temperatures from -70 to 30 ° C.
  • a transition metal catalyst such as, for. B. Pd (Ph3P) 4, PdCl2, Pd (Ph3P) 2Cl2, Pd (PhCN) 2Cl2, Pd (OAc) 2 or Ni (PPh3) 2C
  • the carboxylic acid halides of the general formula IV are either known or can be prepared by processes analogous to known processes. Corresponding manufacturing instructions are described, for example, in Houben-Weyl, Methods of Organic Chemistry, Vol. E5, p. 587.
  • the new compounds are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes and Basidiomycetes. Some of them are systemically effective and can be used as foliar and soil fungicides.
  • the fungicidal compounds are particularly interesting for controlling a large number of fungi on various crop plants or their seeds, in particular wheat, rye, barley, oats, rice, corn, lawn, cotton, soybeans, coffee, sugar cane, fruit and ornamental plants in horticulture and viticulture as well as vegetables - such as cucumbers, beans and pumpkin plants -.
  • the new compounds are particularly suitable for combating the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on different plants, Plasmopara viti
  • the compounds are applied by spraying or dusting the plants with the active compounds or by treating the seeds of the plants with the active compounds. It is used before or after the plants or seeds are infected by the fungi.
  • the fungi or the plants, seeds, materials or the soil to be protected against fungal attack are treated with a fungicidally effective amount of the active ingredient.
  • the new substances can be converted into the usual formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application forms depend entirely on the purposes; in any case, they should ensure a fine and uniform distribution of the active substance.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if appropriate using emulsifiers and dispersants, and if water is used as the diluent, other organic solvents can also be used as auxiliary solvents.
  • solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g.
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates)
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates are between 0.02 and 3 kg of active ingredient or more per hectare.
  • the new compounds can also be used in material protection (wood protection), e.g. against Paecilomyces variotii.
  • material protection wood protection
  • amounts of active ingredient of 0.001 to 50 g, preferably 0.01 to 10 g, are generally required per kilogram of seed.
  • agents or the ready-to-use preparations produced therefrom such as solutions, emulsions, suspensions, powders, dusts, pastes or granules, are used in a known manner, for example by spraying, atomizing, dusting, scattering, pickling or pouring.
  • the agents according to the invention can also be present together with other active ingredients, such as e.g. Herbicides, insecticides, growth regulators and fungicides, or also mixed with fertilizers and applied. When mixed with fungicides, the fungicidal activity spectrum is enlarged in many cases.
  • Pepper seedlings of the "Neusiedler Ideal Elite" variety after 4-5 leaves had developed well, were sprayed to runoff with aqueous suspensions which contained 80% active ingredient and 20% emulsifier in the dry matter. After the spray coating had dried on, the plants were sprayed with a conidia suspension of the botrytis cinerea fungus and placed at 22-24 ° C. in a chamber with high atmospheric humidity. After 5 days the disease had developed so strongly on the untreated control plants that the leaf necrosis formed covered the majority of the leaves.
  • Barley seedlings of the "Igri" variety were sprayed to runoff point in the two-leaf stage with aqueous suspensions containing 80% active ingredient and 20% emulsifier in the dry matter. After 24 hours, the plants were inoculated with a spore suspension of the fungus Pyrenophora teres and placed in a climatic chamber with high atmospheric humidity at 18 ° C. for 48 hours. The plants were then cultivated in a greenhouse at 20-22 ° C. and 70% relative atmospheric humidity for a further 5 days. The extent of leaf infestation was then determined.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Claims (7)

  1. Benzylcétones de formule générale I dans laquelle
    X   représente CH ou N,
    Y   représente O ou NR⁴,
    R¹, R²   représentent H ou un groupe en C1-C4;
    R³   représente H, un halogène, un groupe cyano, nitro, alkyle en C1-C6, cycloalkyle en C3-C6, alcoxy en C1-C6, halogénoalkyle en C1-C2, aryl-alkyle en C1-C2, aryl-alcoxy en C1-C2, aryloxy ou aryle, les groupes aryle pouvant eux-mêmes porter un à trois substituants choisis parmi les halogènes, les groupes cyano, nitro, alkyle en C1-C6, alcoxy en C1-C6 ou halogénoalkyle en C1-C2,
    R⁴   représente OH, un groupe alcoxy en C1-C6 ou aryl-alcoxy en C1-C2 et
    R⁵   représente H, un groupe méthyle, un halogène ou un groupe méthoxy.
  2. Produits fongicides contenant un véhicule inerte et une quantité fongicide efficace d'un composé de formule I dans laquelle
    X   représente CH ou N,
    Y   représente O ou NR⁴,
    R¹, R²   représentent H ou un groupe alkyle en C1-C4,
    R³   représente H, un halogène, un groupe cyano, nitro, alkyle en C1-C6, cycloalkyle en C3-C6, alcoxy en C1-C6, halogénoalkyle en C1-C2, aryl-alkyle en C1-C2, aryl-alcoxy en C1-C2, aryloxy ou aryle, les groupes aryle pouvant eux-mêmes porter un à trois substituants choisis parmi les halogènes, les groupes cyano, nitro, alkyle en C1-C6, alcoxy en C1-C6 ou halogénoalkyle en C1-C2,
    R⁴   représente OH, un groupe alcoxy en C1-C6 ou aryl-alcoxy en C1-C2 et
    R⁵   représente H, un groupe méthyle, un halogène ou un groupe méthoxy.
  3. Procédé pour combattre les mycètes, caractérisé en ce que l'on traite les mycètes ou les végétaux, semences, matériaux ou surfaces menacés d'une attaque par les mycètes, par une quantité fongicide efficace d'un composé de formule I dans laquelle
    X   représente CH ou N,
    Y   représente O ou NR⁴,
    R¹, R²   représentent H ou un groupe alkyle en C1-C4,
    R³   représente H, un halogène, un groupe cyano, nitro, alkyle en C1-C6, cycloalkyle en C3-C6, alcoxy en C1-C6, halogénoalkyle en C1-C2, aryl-alkyle en C1-C2, aryl-alcoxy en C1-C2, aryloxy ou aryle, les groupes aryle pouvant eux-mêmes porter un à trois substituants choisis parmi les halogènes, les groupes cyano, nitro, alkyle en C1-C6, alcoxy en C1-C6 ou halogénoalkyle en C1-C2,
    R⁴   représente OH, un groupe alcoxy en C1-C6 ou aryl-alcoxy en C1-C2 et
    R⁵   représente H, un groupe méthyle, un halogène ou un groupe méthoxy.
  4. Composé de formule I selon la revendication 1, dans laquelle R¹ et R² représentent des groupes méthyle, Y représente O, X représente CH et R³ l'hydrogène.
  5. Composé de formule I selon la revendication 1, dans laquelle R¹ et R² représentent des groupes méthyle, Y représente O, X représente N et R³ un groupe méthyle en position 2.
  6. Composé de formule I selon la revendication 1, dans laquelle R¹ et R² représentent des groupes méthyle, Y représente O, X représente CH et R³ un groupe méthyle en position 2.
  7. Procédé de préparation des benzylcétones de formule générale I dans laquelle
    X   représente CH ou N,
    Y   représente O ou NR⁴,
    R¹, R²   représentent H ou un groupe alkyle en C1-C4,
    R³   représente H, un halogène, un groupe cyano, nitro, alkyle en C1-C6, cycloalkyle en C3-C6, alcoxy en C1-C6, halogénoalkyle en C1-C2, aryl-alkyle en C1-C2, aryl-alcoxy en C1-C2, aryloxy ou aryle, les groupes aryle pouvant eux-mêmes porter un à trois substituants choisis parmi les halogènes, les groupes cyano, nitro, alkyle en C1-C6, alcoxy en C1-C6 ou halogénoalkyle en C1-C2,
    R⁴   représente OH, un groupe alcoxy en C1-C6 ou aryl-alcoxy en C1-C2 et
    R⁵   représente H, un groupe méthyle, un halogène ou un groupe méthoxy,
    caractérisé en ce que l'on convertit un halogénure de benzyle de formule générale II, à l'aide du zinc et de CuCN.2LiCl, en un composé organique de zinc-cuivre de formule générale III qu'on fait ensuite réagir avec les halogénures d'acides carboxyliques de formule IV X, R¹, R² et R³ ayant les significations indiquées ci-dessus, Hal représentant un halogéne, et le cas échéant on fait réagir les cétones ainsi obtenues avec une amine de structure générale NH₂R⁴ dans laquelle R⁴ a les significations indiquées ci-dessus.
EP91109806A 1990-06-27 1991-06-14 Benzylecétones et fongicides les contenant Expired - Lifetime EP0463513B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4020397 1990-06-27
DE4020397A DE4020397A1 (de) 1990-06-27 1990-06-27 Benzylketone und diese enthaltende fungizide

Publications (3)

Publication Number Publication Date
EP0463513A2 EP0463513A2 (fr) 1992-01-02
EP0463513A3 EP0463513A3 (en) 1992-10-07
EP0463513B1 true EP0463513B1 (fr) 1995-04-12

Family

ID=6409146

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91109806A Expired - Lifetime EP0463513B1 (fr) 1990-06-27 1991-06-14 Benzylecétones et fongicides les contenant

Country Status (15)

Country Link
US (1) US5147892A (fr)
EP (1) EP0463513B1 (fr)
JP (1) JPH04230234A (fr)
KR (1) KR920000688A (fr)
AT (1) ATE121071T1 (fr)
AU (1) AU630819B2 (fr)
CA (1) CA2045044A1 (fr)
DE (2) DE4020397A1 (fr)
DK (1) DK0463513T3 (fr)
ES (1) ES2071167T3 (fr)
GR (1) GR3015774T3 (fr)
HU (1) HU208665B (fr)
IL (1) IL98628A (fr)
NZ (1) NZ238713A (fr)
ZA (1) ZA914916B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW224042B (fr) 1992-04-04 1994-05-21 Basf Ag
US20070111519A1 (en) * 2003-10-15 2007-05-17 Applied Materials, Inc. Integrated electroless deposition system

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3623921A1 (de) * 1986-07-16 1988-01-21 Basf Ag Oximether und diese enthaltende fungizide
ES2059527T3 (es) * 1987-09-09 1994-11-16 Zeneca Ltd Fungicidas.
DE3816577A1 (de) * 1988-05-14 1989-11-16 Basf Ag Acrylester und diese enthaltende fungizide
DE3827361A1 (de) * 1988-08-12 1990-03-01 Basf Ag Oximether, verfahren zu ihrer herstellung und diese verbindungen enthaltende fungizide
IL93765A (en) * 1989-04-11 1995-08-31 Basf Ag Oxirane Phenyl Esters and fungicides containing them

Also Published As

Publication number Publication date
EP0463513A3 (en) 1992-10-07
AU7929591A (en) 1992-01-02
ES2071167T3 (es) 1995-06-16
ATE121071T1 (de) 1995-04-15
DE59105144D1 (de) 1995-05-18
CA2045044A1 (fr) 1991-12-28
HUT58034A (en) 1992-01-28
DK0463513T3 (da) 1995-06-26
ZA914916B (en) 1993-03-31
HU912140D0 (en) 1991-12-30
KR920000688A (ko) 1992-01-29
JPH04230234A (ja) 1992-08-19
DE4020397A1 (de) 1992-01-02
GR3015774T3 (en) 1995-07-31
IL98628A0 (en) 1992-07-15
AU630819B2 (en) 1992-11-05
IL98628A (en) 1995-05-26
NZ238713A (en) 1992-06-25
US5147892A (en) 1992-09-15
HU208665B (en) 1993-12-28
EP0463513A2 (fr) 1992-01-02

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